diff --git a/jOOQ/src/main/java/org/jooq/conf/Settings.java b/jOOQ/src/main/java/org/jooq/conf/Settings.java
index e53a77b7d4..ec18a421d7 100644
--- a/jOOQ/src/main/java/org/jooq/conf/Settings.java
+++ b/jOOQ/src/main/java/org/jooq/conf/Settings.java
@@ -493,6 +493,8 @@ public class Settings
     protected Boolean migrationIgnoreDefaultTimestampPrecisionDiffs = true;
     @XmlElement(defaultValue = "false")
     protected Boolean migrationIgnoreUnnamedConstraintDiffs = false;
+    @XmlElement(defaultValue = "true")
+    protected Boolean migrationIgnoreImplicitPrimaryKeyNotNullConstraints = true;
     @XmlElement(type = String.class)
     @XmlJavaTypeAdapter(LocaleAdapter.class)
     protected Locale locale;
@@ -6338,6 +6340,30 @@ public class Settings
         this.migrationIgnoreUnnamedConstraintDiffs = value;
     }
 
+    /**
+     * Various <code>migrateTo()</code> methods (e.g. {@link org.jooq.Meta#migrateTo(org.jooq.Meta)}) ignore the presence or absence of implicit <code>NOT NULL</code> constraints on <code>PRIMARY KEY</code> columns. This flag allows for overriding this behaviour.
+     * 
+     * @return
+     *     possible object is
+     *     {@link Boolean }
+     *     
+     */
+    public Boolean isMigrationIgnoreImplicitPrimaryKeyNotNullConstraints() {
+        return migrationIgnoreImplicitPrimaryKeyNotNullConstraints;
+    }
+
+    /**
+     * Various <code>migrateTo()</code> methods (e.g. {@link org.jooq.Meta#migrateTo(org.jooq.Meta)}) ignore the presence or absence of implicit <code>NOT NULL</code> constraints on <code>PRIMARY KEY</code> columns. This flag allows for overriding this behaviour.
+     * 
+     * @param value
+     *     allowed object is
+     *     {@link Boolean }
+     *     
+     */
+    public void setMigrationIgnoreImplicitPrimaryKeyNotNullConstraints(Boolean value) {
+        this.migrationIgnoreImplicitPrimaryKeyNotNullConstraints = value;
+    }
+
     /**
      * The Locale to be used with any locale dependent logic if there is not a more specific locale available. More specific locales include e.g. {@link #getRenderLocale()}, {@link #getParseLocale()}, or {@link #getInterpreterLocale()}.
      * 
@@ -9411,6 +9437,15 @@ public class Settings
         return this;
     }
 
+    /**
+     * Various <code>migrateTo()</code> methods (e.g. {@link org.jooq.Meta#migrateTo(org.jooq.Meta)}) ignore the presence or absence of implicit <code>NOT NULL</code> constraints on <code>PRIMARY KEY</code> columns. This flag allows for overriding this behaviour.
+     * 
+     */
+    public Settings withMigrationIgnoreImplicitPrimaryKeyNotNullConstraints(Boolean value) {
+        setMigrationIgnoreImplicitPrimaryKeyNotNullConstraints(value);
+        return this;
+    }
+
     /**
      * The Locale to be used with any locale dependent logic if there is not a more specific locale available. More specific locales include e.g. {@link #getRenderLocale()}, {@link #getParseLocale()}, or {@link #getInterpreterLocale()}.
      * 
@@ -9927,6 +9962,7 @@ public class Settings
         builder.append("migrationAutoVerification", migrationAutoVerification);
         builder.append("migrationIgnoreDefaultTimestampPrecisionDiffs", migrationIgnoreDefaultTimestampPrecisionDiffs);
         builder.append("migrationIgnoreUnnamedConstraintDiffs", migrationIgnoreUnnamedConstraintDiffs);
+        builder.append("migrationIgnoreImplicitPrimaryKeyNotNullConstraints", migrationIgnoreImplicitPrimaryKeyNotNullConstraints);
         builder.append("locale", locale);
         builder.append("parseDialect", parseDialect);
         builder.append("parseLocale", parseLocale);
@@ -11821,6 +11857,15 @@ public class Settings
                 return false;
             }
         }
+        if (migrationIgnoreImplicitPrimaryKeyNotNullConstraints == null) {
+            if (other.migrationIgnoreImplicitPrimaryKeyNotNullConstraints!= null) {
+                return false;
+            }
+        } else {
+            if (!migrationIgnoreImplicitPrimaryKeyNotNullConstraints.equals(other.migrationIgnoreImplicitPrimaryKeyNotNullConstraints)) {
+                return false;
+            }
+        }
         if (locale == null) {
             if (other.locale!= null) {
                 return false;
@@ -12285,6 +12330,7 @@ public class Settings
         result = ((prime*result)+((migrationAutoVerification == null)? 0 :migrationAutoVerification.hashCode()));
         result = ((prime*result)+((migrationIgnoreDefaultTimestampPrecisionDiffs == null)? 0 :migrationIgnoreDefaultTimestampPrecisionDiffs.hashCode()));
         result = ((prime*result)+((migrationIgnoreUnnamedConstraintDiffs == null)? 0 :migrationIgnoreUnnamedConstraintDiffs.hashCode()));
+        result = ((prime*result)+((migrationIgnoreImplicitPrimaryKeyNotNullConstraints == null)? 0 :migrationIgnoreImplicitPrimaryKeyNotNullConstraints.hashCode()));
         result = ((prime*result)+((locale == null)? 0 :locale.hashCode()));
         result = ((prime*result)+((parseDialect == null)? 0 :parseDialect.hashCode()));
         result = ((prime*result)+((parseLocale == null)? 0 :parseLocale.hashCode()));
diff --git a/jOOQ/src/main/java/org/jooq/impl/Diff.java b/jOOQ/src/main/java/org/jooq/impl/Diff.java
index e444cf9b97..bc3ed22903 100644
--- a/jOOQ/src/main/java/org/jooq/impl/Diff.java
+++ b/jOOQ/src/main/java/org/jooq/impl/Diff.java
@@ -299,7 +299,7 @@ final class Diff {
 
                 // TODO: The order of dropping / adding these objects might be incorrect
                 //       as there could be inter-dependencies.
-                appendColumns(r, t1, asList(t1.fields()), asList(t2.fields()));
+                appendColumns(r, t1, t2, asList(t1.fields()), asList(t2.fields()));
                 appendPrimaryKey(r, t1, asList(t1.getPrimaryKey()), asList(t2.getPrimaryKey()));
                 appendUniqueKeys(r, t1, removePrimary(t1.getKeys()), removePrimary(t2.getKeys()));
                 appendForeignKeys(r, t1, t1.getReferences(), t2.getReferences());
@@ -373,7 +373,13 @@ final class Diff {
         return false;
     }
 
-    private final DiffResult appendColumns(DiffResult result, Table<?> t1, List<? extends Field<?>> l1, List<? extends Field<?>> l2) {
+    private final DiffResult appendColumns(
+        DiffResult result,
+        Table<?> t1,
+        Table<?> t2,
+        List<? extends Field<?>> l1,
+        List<? extends Field<?>> l2
+    ) {
         final List<Field<?>> add = new ArrayList<>();
         final List<Field<?>> drop = new ArrayList<>();
 
@@ -413,9 +419,9 @@ final class Diff {
                     if (typeNameDifference(type1, type2))
                         r.queries.add(ctx.alterTable(t1).alter(f1).set(type2.nullability(Nullability.DEFAULT)));
 
-                    if (type1.nullable() && !type2.nullable())
+                    if (type1.nullable() && !type2.nullable() && respectPkNullability(f1, f2))
                         r.queries.add(ctx.alterTable(t1).alter(f1).setNotNull());
-                    else if (!type1.nullable() && type2.nullable())
+                    else if (!type1.nullable() && type2.nullable() && respectPkNullability(f1, f2))
                         r.queries.add(ctx.alterTable(t1).alter(f1).dropNotNull());
 
                     Field<?> d1 = type1.defaultValue();
@@ -435,6 +441,19 @@ final class Diff {
                     // [#9656] TODO: Change character set
                 }
 
+                private final boolean respectPkNullability(Field<?> f1, Field<?> f2) {
+                    if (FALSE.equals(ctx.settings().isMigrationIgnoreImplicitPrimaryKeyNotNullConstraints()))
+                        return true;
+
+                    UniqueKey<?> pk1 = t1.getPrimaryKey();
+                    UniqueKey<?> pk2 = t2.getPrimaryKey();
+
+                    return pk1 == null
+                        || pk2 == null
+                        || !pk1.getFields().contains(f1)
+                        || !pk2.getFields().contains(f2);
+                }
+
                 private final boolean typeNameDifference(DataType<?> type1, DataType<?> type2) {
                     if (type1.getTypeName().equals(type2.getTypeName()))
                         return false;
diff --git a/jOOQ/src/main/resources/org/jooq/xsd/jooq-runtime-3.20.0.xsd b/jOOQ/src/main/resources/org/jooq/xsd/jooq-runtime-3.20.0.xsd
index 9b37e42e80..2da5409dea 100644
--- a/jOOQ/src/main/resources/org/jooq/xsd/jooq-runtime-3.20.0.xsd
+++ b/jOOQ/src/main/resources/org/jooq/xsd/jooq-runtime-3.20.0.xsd
@@ -1568,6 +1568,10 @@ deployed on an RDBMS that does not.]]></jxb:javadoc></jxb:property></appinfo></a
         <annotation><appinfo><jxb:property><jxb:javadoc><![CDATA[Various <code>migrateTo()</code> methods (e.g. {@link org.jooq.Meta#migrateTo(org.jooq.Meta)}) ignore the difference between (possibly synthetically) name constraints and unnamed constraints, if the structure of the constraint is the same.]]></jxb:javadoc></jxb:property></appinfo></annotation>
       </element>
       
+      <element name="migrationIgnoreImplicitPrimaryKeyNotNullConstraints" type="boolean" minOccurs="0" maxOccurs="1" default="true">
+        <annotation><appinfo><jxb:property><jxb:javadoc><![CDATA[Various <code>migrateTo()</code> methods (e.g. {@link org.jooq.Meta#migrateTo(org.jooq.Meta)}) ignore the presence or absence of implicit <code>NOT NULL</code> constraints on <code>PRIMARY KEY</code> columns. This flag allows for overriding this behaviour.]]></jxb:javadoc></jxb:property></appinfo></annotation>
+      </element>
+      
       <element name="locale" type="string" minOccurs="0" maxOccurs="1">
         <annotation><appinfo><jxb:property><jxb:javadoc><![CDATA[The Locale to be used with any locale dependent logic if there is not a more specific locale available. More specific locales include e.g. {@link #getRenderLocale()}, {@link #getParseLocale()}, or {@link #getInterpreterLocale()}.]]></jxb:javadoc></jxb:property></appinfo></annotation>
       </element>